NPASS Compound

Natural Product: NPC116714

Natural Product ID	NPC116714
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZZIQOLQUNMQKEU-QSEDHFBNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 72 76 0 0 0 0 0 0 0 0999 V2000 -4.4262 -5.7323 1.3234 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1799 -5.2136 0.9266 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0368 -3.8719 0.5578 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1572 -3.0743 0.5958 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0840 -1.7418 0.2449 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8768 -1.1714 -0.1562 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8252 0.1621 -0.4985 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7659 0.7023 -0.8584 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9884 0.9010 -0.4332 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1451 0.2893 -0.0336 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3932 1.0023 0.0574 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5475 0.3305 0.4476 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7262 1.0246 0.5382 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8234 2.3559 0.2617 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6942 3.0221 -0.1222 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4802 2.3422 -0.2235 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7494 4.3696 -0.4106 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0131 3.0369 0.3574 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1500 -0.9900 0.2855 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7242 -1.9548 -0.2048 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8714 -3.3198 0.1706 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5672 -1.4949 -0.5657 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5897 -1.0322 -0.9275 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4070 -2.0577 -1.6773 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5844 -2.6097 -0.9840 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3077 -1.6936 -0.0412 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6392 -0.3540 -0.1202 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2423 0.7300 0.6892 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5605 0.9896 0.4209 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0266 2.0444 1.2034 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4212 3.1561 0.2809 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8670 3.5457 0.3555 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 2.4113 0.6408 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2120 1.3510 1.5220 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0130 1.6830 2.1039 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1904 1.7868 -0.5612 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9927 4.5615 1.3057 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1286 2.8362 -1.0634 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2953 -0.5820 0.2219 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6649 -1.6231 -0.3423 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2319 -3.8128 -0.3236 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7982 -1.4963 -2.8881 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1086 -5.6098 0.4340 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7706 -5.1474 2.1974 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2889 -6.8047 1.5655 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0994 -3.4816 0.8981 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9202 1.9391 -0.7069 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5113 -0.7177 0.6719 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6404 0.5020 0.8448 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6302 2.9355 -0.5317 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7621 4.7428 -1.3616 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0640 4.0405 0.2328 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9649 -3.9261 0.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5516 -0.0820 -1.5449 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7293 -2.9156 -1.9563 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3508 -2.9620 -1.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1874 -2.1212 0.9986 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6077 -0.0810 -1.2156 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6656 1.6657 0.4581 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0407 0.5184 1.7658 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1799 2.4306 1.8507 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8339 4.1026 0.4692 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1472 3.9852 -0.6394 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7379 2.8559 1.0521 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1481 0.3580 1.0231 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9419 1.1971 2.3709 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9769 1.2040 -0.3959 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2766 5.4276 0.8872 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7546 2.1572 -1.4185 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7188 -1.2662 -1.2826 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1510 -4.5439 -0.9930 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0191 -1.2114 -3.4362 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 14 18 1 0 10 19 1 0 6 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 31 38 1 0 27 39 1 0 26 40 1 0 25 41 1 0 24 42 1 0 21 3 1 0 39 23 1 0 19 5 1 0 35 30 1 0 16 11 1 0 1 43 1 0 1 44 1 0 1 45 1 0 4 46 1 0 9 47 1 0 12 48 1 0 13 49 1 0 16 50 1 0 17 51 1 0 18 52 1 0 21 53 1 0 23 54 1 6 24 55 1 6 25 56 1 6 26 57 1 1 27 58 1 6 28 59 1 0 28 60 1 0 30 61 1 1 31 62 1 1 32 63 1 6 33 64 1 1 34 65 1 0 34 66 1 0 36 67 1 0 37 68 1 0 38 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	ZZIQOLQUNMQKEU-QSEDHFBNSA-N
Standard InCHI	InChI=1S/C27H30O15/c1-37-11-5-17-20(14(30)7-16(40-17)10-2-3-12(28)13(29)4-10)18(6-11)41-27-25(36)23(34)22(33)19(42-27)9-39-26-24(35)21(32)15(31)8-38-26/h2-7,15,19,21-29,31-36H,8-9H2,1H3/t15-,19+,21+,22+,23-,24-,25+,26-,27+/m1/s1
SMILES	COc1cc2c(c(=O)cc(c3ccc(c(c3)O)O)o2)c(c1)O[C@@H]1[C@H]([C@@H]([C@H]([C@H](CO[C@@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	0.282 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.819 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.156 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	238.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.146	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.644	Fsp³:	0.444
MCE-18:	115.923 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.642	Fluc inhibitor:	0.28 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.973 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.863 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.058	Promiscuous compounds:	0.335

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.378	MDCK Permeability:	-5.273
Pgp-inhibitor:	0.0	Pgp-substrate:	0.432
PAMPA:	0.998 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.214
20% Bioavailability (F20%):	0.691	30% Bioavailability (F30%):	0.966
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.078
Plasma Protein Binding (PPB):	78.867%	Volume Distribution (VD):	-0.092
Fu:	18.677% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.628
BSEP inhibitor:	0.098

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.14 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.418

Half-life (T1/2):

4.492

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.305
Human Hepatotoxicity (H-HT):	0.453	Drug-induced Liver Injury (DILI):	0.937
AMES Toxicity:	0.687	Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.407	Skin Sensitization:	0.987
Carcinogencity:	0.052	Eye Corrosion:	0.0
Eye Irritation:	0.866	Respiratory Toxicity:	0.041
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.906
Hematotoxicity:	0.07	Drug-induced Nephrotoxicity:	0.468
Genotoxicity:	0.708	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.364	Hek293 Cytotoxicity:	0.147
BCF:	0.476 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.165 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.836 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.017 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6737	Psacalium radulifolium	Species	Asteraceae	Eukaryota	roots	n.a.	n.a.	PMID[11325222]
NPO5829	Distylium racemosum	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21489793]
NPO5829	Distylium racemosum	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6737	Psacalium radulifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5829	Distylium racemosum	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10383	Viguiera hypochlora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8320	Cryptostylis erythroglossa	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6737	Psacalium radulifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC116714 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	23086
0.1-0.2	23099
0.2-0.3	2709
0.3-0.4	618
0.4-0.5	272
0.5-0.6	49
0.6-0.7	12
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9012	High Similarity	NPC129827
0.878	High Similarity	NPC473512
0.8313	Intermediate Similarity	NPC295613
0.8095	Intermediate Similarity	NPC473657
0.8	Intermediate Similarity	NPC15358
0.7931	Intermediate Similarity	NPC284277
0.7727	Intermediate Similarity	NPC475497
0.6596	Remote Similarity	NPC475366
0.6559	Remote Similarity	NPC210073
0.6452	Remote Similarity	NPC301683
0.6364	Remote Similarity	NPC610763
0.6354	Remote Similarity	NPC65711
0.6344	Remote Similarity	NPC236191
0.6304	Remote Similarity	NPC52353
0.6264	Remote Similarity	NPC293004
0.625	Remote Similarity	NPC488074
0.617	Remote Similarity	NPC51774
0.6105	Remote Similarity	NPC67326
0.6064	Remote Similarity	NPC254540
0.5938	Remote Similarity	NPC44931
0.5806	Remote Similarity	NPC284960
0.58	Remote Similarity	NPC209296
0.5714	Remote Similarity	NPC22062
0.5714	Remote Similarity	NPC473634
0.5714	Remote Similarity	NPC138811
0.567	Remote Similarity	NPC471079
0.5644	Remote Similarity	NPC229409
0.5612	Remote Similarity	NPC142996
0.5612	Remote Similarity	NPC67105
0.5604	Remote Similarity	NPC110349
0.5591	Remote Similarity	NPC182045
0.55	Remote Similarity	NPC204693
0.549	Remote Similarity	NPC51326
0.5464	Remote Similarity	NPC172807
0.5437	Remote Similarity	NPC488089
0.5437	Remote Similarity	NPC600130
0.5435	Remote Similarity	NPC19709
0.54	Remote Similarity	NPC102028
0.5392	Remote Similarity	NPC470443
0.5385	Remote Similarity	NPC231194
0.5377	Remote Similarity	NPC244875
0.5376	Remote Similarity	NPC168822
0.5376	Remote Similarity	NPC189142
0.5376	Remote Similarity	NPC77660
0.5361	Remote Similarity	NPC194483
0.5361	Remote Similarity	NPC190003
0.534	Remote Similarity	NPC473623
0.534	Remote Similarity	NPC483707
0.5333	Remote Similarity	NPC101636
0.5319	Remote Similarity	NPC45638
0.5294	Remote Similarity	NPC488073
0.5294	Remote Similarity	NPC126784
0.5294	Remote Similarity	NPC241423
0.5263	Remote Similarity	NPC201292
0.5248	Remote Similarity	NPC203259
0.5248	Remote Similarity	NPC33054
0.5248	Remote Similarity	NPC245059
0.5248	Remote Similarity	NPC176740
0.5248	Remote Similarity	NPC471725
0.5248	Remote Similarity	NPC134532
0.5248	Remote Similarity	NPC156869
0.5248	Remote Similarity	NPC602582
0.5204	Remote Similarity	NPC61791
0.5196	Remote Similarity	NPC186816
0.5152	Remote Similarity	NPC211594
0.5146	Remote Similarity	NPC64051
0.5106	Remote Similarity	NPC83283
0.5047	Remote Similarity	NPC298171

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC116714 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5604
0.1-0.2	3478
0.2-0.3	56
0.3-0.4	7
0.4-0.5	1
0.5-0.6	3
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6735	Remote Similarity	NPD7472	Pre-clinical
0.58	Remote Similarity	NPD7054	Phase 4
0.5385	Remote Similarity	NPD7251	Phase 2
0.5248	Remote Similarity	NPD6797	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data